Sodium Bromide → Benzyl (4-oxotetrahydrofuran-3-yl)carbamate

HRID 413229Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 413229
C(=O)(O)[O-].[Na+].[OH:6][CH:7]1[CH:11]([NH:12][C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])[CH2:10][O:9][CH2:8]1.[Br-].[Na+].CC1(C)N([O])C(C)(C)CCC1>CCOC(C)=O.C1(C)C=CC=CC=1.O>[CH2:16]([O:15][C:13]([NH:12][CH:11]1[CH2:10][O:9][CH2:8][C:7]1=[O:6])=[O:14])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Komponenten

8

Edukt 4

HCID 253881Sodium BromideHCID 516892Sodium BicarbonateHCID 2724126TempoHCID 18523488Benzyl (3S,4S)-4-hydroxytetrahydrofuran-3-ylcarbamate

Produkt 1

HCID 18523485Benzyl (4-oxotetrahydrofuran-3-yl)carbamate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of bleach (100 ml), containing sodium bicarbonate (7.34 g), was added dropwise to a rapidly stirred mixture of 3-hydroxy-4-benzyloxycarbonylamino-tetrahydrofuran (21 g, 88 mmol), sodium bromide (9.4 g), TEMPO (50 mg) in EtOAc (140 ml), toluene (140 ml) and water (40 ml). After a persistant orange colour developed the mixture was extracted with EtOAc and the combined organic layers were washed with saturated sodium bicarbonate, brine and dried (MgSO4). Evaporation under reduced pressure and purification of the residue by column chromatography afforded the title compound as white crystals, 18 g, 87%.

Aufarbeitung

  1. extractionwas extracted with EtOAc
  2. washthe combined organic layers were washed with saturated sodium bicarbonate, brine
  3. dry with materialdried (MgSO4)
  4. customEvaporation
  5. customunder reduced pressure and purification of the residue by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-2b719e8a22314a7f990850f28486915f
Quelldatensatz
uspto-grants-2003_05
Patentnummer
US06566373B2

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